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5 Pillars We Live And Die By

What values do you live by? Do you find they’re the same as the ones you rely on to navigate the professional world? Or are you a different person at work and in life? In my experience, those worlds have to intersect, and the lessons you learn in each of them should make you better in the other. I talk a lot about life experiences, especially failure, being the greatest teacher you will meet. Over my career, my many experiences with founding and growing and successfully exiting (and also shuttering and getting fired from) tech startups, I’ve had what feels like multiple lives worth of experience. Over time, that experience has distilled down into 5 pillars that I live by, work by, and die by, and which I run MacDonald Ventures by, too. Here they are.

5 Pillars For Living A Fearless Life 

1. Face Challenges With Confidence And Courage

Don’t be afraid of failure. But it’s not enough to just be unafraid, or even ready. You have to actively seek out opportunities where you could fail. Run towards the thing that scares you, that pushes you, and challenges you. It’s not just an attitude needed for business, but your whole life. Pushing yourself outside of your comfort zone teaches you that being afraid won’t kill you, it won’t even hurt you. And increasing your resilience in one area will bleed over beneficially into other areas of your life. Wouldn’t you rather work through your discomfort cruising 15mph down Silverton Mountain than when you’re trying to keep a steady hand in your pitch meeting?

Discomfort means you’re getting better. Fear is growth. Keep pushing. Never stop pushing.

2. Ask Many Questions With An Open Mind 

When you’re in conversation with someone about your startup, are you mostly talking or mostly listening? Do you find you’re thinking of what you’re going to say next while the other person is talking? Reworking your angle on your pitch to convince them? Maybe even dismissing them – “they just don’t get it.” We are all guilty of this and, sometimes, we all need to shut up a little bit. It’s natural as founders to get focused on the sell, to capture a willing ear, to share our passion. And there’s a place for that. But there’s also a time to learn and connect and you do that by asking questions.

Everyone you interact with has something to teach you. From business mentors to your next potential client and beta tester, you need to approach moments where you are receiving feedback without bias and with a calm, inquisitive nature. When you feel yourself becoming sensitive to criticism and are preparing to launch into your well-worn pitch, stop. You’re no longer listening and that feeling of anxiety, stress, defensiveness – it’s a jail cell that will make you miss the information you need and keep you small.

We are the center of our own universe. It takes active work to force an outside perspective on ourselves – we are not naturally good at this. You get better at it by asking questions. Start practicing this in your everyday life and you’ll be shocked at how much easier and more pleasant it becomes to have conversations you used to avoid.

3. Knowledge Is Power, But Not Without Action. 

In theory, there are an infinite number of incredible insights that could revolutionize the world. But, theories don’t create change, action creates change. There’s a big difference between working on a theoretical solution and taking the hard, frustrating, sometimes tedious, and often very long-term actions necessary to bring an idea to market. And that’s not even the finish line. Once you’re there, you’ve got to learn from your customers, your investors, your partners. You have to iterate, tear down, rebuild. If all you’re bringing to the table is a theory, you’ll get eaten alive or completely ignored. I often find that startup founders aren’t the stereotypical “smartest guy in the room,” the guy who went to a big-name business school. They’re just willing to do the work and take the steps, one after the other, to get where they need to go to succeed.

How many people have you heard say “I had that idea,” about a genius solution that is making some other guy millions of dollars (a guy who actually did something with his idea)? 

You want to be the second guy. 

4. Inspire Greatness

Who are you inspired by? Your first thoughts probably drifted over famous names, right? Business leaders, past-Presidents, figures from history? Wrong. When I say “inspire,” I mean it literally: who, through direct experiences in your life, has caused you to change in some pivotal way, urged you to action, was instrumental in your path, altered the way you saw yourself? Chances are these people are largely regular people, people without speechwriters, handlers, or historians helping them seem great. Our childhood teachers, professors, direct managers, business mentors, colleagues, partners, even our children – these people have a profound impact on our lives daily.

And that means, in turn, we have the opportunity to inspire greatness and lead others every day. Whether you are founding a startup with 3 team members or preparing to exit a 500-person company, you have the same opportunity to inspire others and to continue to expose yourself to inspiring people.

The goal should be to be an integral part of a never-ending cycle of motivation, fueling your desire to achieve your goals while helping others do the same.  

You will be shocked, as I have been, how much more meaningful life is when you get to be a part of helping others see the greatness in themselves and achieve their dreams in business and life.

5. Have An Attitude Of Gratitude

When I advise founders, I always say, “enjoy the ride,” and I mean it sincerely. What is the point of any of this – the struggle, the challenge, the hard work – if we take it for granted, if we focus on a meaningless finish line that doesn’t exist? That saying – enjoy the ride – came to me about halfway through my career, when I realized I was starting to see the universe from a different perspective when the hard times started to feel just as rewarding as the rewards themselves. This is an incredibly freeing, motivating, exciting place to live. You can get there too. 

Life is fragile. We have to make the effort to be grateful for what we have so we don’t take it for granted. My wife, Lindsay, is a gratitude-bully (the best kind of bully), and she is the person I credit with teaching me, and our son, that you can’t feel gratitude and pessimism at the same time. It’s our family mantra and I’ve seen the impact it has had on us and, when you start to embrace it, the impact it has on those around you.

Don’t miss the joy in the hard times – it’s in there, and you’ll look back with regret if you don’t soak it in.

What Values Do You Live By?

Think about it. Write them down. Are they the right ones? Are they leading you down a safe, comfortable path? Or are they supporting you as you stretch yourself for something greater – pushing you to provide your unique gift to the world? Don’t have business goals and life goals. Have values that push you to be better, more creative, more daring, a bigger thinker, a more inspiring leader, a better partner, and a friend. That will serve you in business and in life, which is just life. And, when you’re ready, I want to hear how to put those values into practice and create a tech solution that is ready to change the world.

But, before that happens and, most importantly:

Enjoy the ride.